1
Supplementary Material
Copper nanoparticles supported on silica coated maghemite as versatile, magnetically
recoverable and reusable catalyst for alkyne coupling and cycloadditon reactions.
F. Nador a, M. A. Volpe b, F. Alonsoc, A. Feldhoff,d A. Kirschning d, G. Radivoy a,*
a
Instituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Av. Alem 1253, 8000 Bahía
Blanca, Argentina
b
c
Planta Piloto de Ingeniería Química, PLAPIQUI (CONICET-UNS), Camino La Carrindanga Km 7, CC 717, 8000 Bahía Blanca Argentina
Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, E-03080,
Alicante, Spain
d
Institut für Organische Chemie and Zentrum für Biomolekulare Wirkstoffe (BMWZ), Leibniz Universit€at Hannover, Schneiderberg 1B, D-30167
Hannover, Germany
Index
1. General
1
2. Compound characterization data
2
3. References
15
1. General
Copper(II) chloride dihydrate (Aldrich), lithium powder (MEDALCHEMY S. L.), and DTBB (4,4'di-tert-butylbiphenyl, Aldrich) were commercially available. CuCl2·2H2O was dehydrated
immediately before use by heating in oven at 150ºC. All the starting materials and other reagents
were commercially available of the best grade (Aldrich, Fluka, Merck) and were used without
further purification. Anhydrous THF was freshly distilled from sodium/benzophenone ketyl. Other
solvents used were treated prior to use by standard methods. NMR spectra were recorded on Bruker
Avance 300 spectrometer (300 MHz for 1H NMR, and 75 MHz for 13C NMR, respectively) using
CDCl3 as solvent (unless otherwise stated) and TMS as internal standard; chemical shifts are given
in  (ppm) and coupling constants (J) in Hertz. Mass spectra (EI) were obtained at 70 eV on an
Agilent 5973 spectrometer, fragment ions in m/z with relative intensities (%) in parenthesis. HRMS
analyses were carried out on a Finnigan MAT95S spectrometer. The purity of volatile compounds
and the chromatographic analyses (GLC) were determined with a Hewlett Packard HP-6890
instrument equipped with a flame ionization detector and a 30 m capillary column (0.32 mm
diameter, 0.25 m film thickness), using nitrogen (2 mL/min) as carrier gas. Thin layer
2
chromatography was carried out on TLC aluminium sheets with silica gel 60 F254 (Merck). Column
chromatography was performed using silica gel 60 of 40–60 microns (hexane/EtOAc as eluant).
TEM images were recorded using a JEOL JEM-2100-F-UHR microscope, operated at an
acceleration voltage of 200 kV. For their observation, the samples were mounted on holey-carbon
coated 300 mesh gold- or copper grids. A pre-treatment of the samples was necessary in order to
improve the observation of the CuNPs deposited on the support. Thus, the catalyst samples were
placed in a Parr reactor and heated to 300º C for 2 hours under flowing hydrogen (1.2 bar). Then,
the reactor was allowed to cool to ambient temperature, the catalyst was suspended in hexane and a
drop of this suspension was added to the grid allowing the solvent to evaporate before being
introduced into the microscope. The XRD diagrams were collected in the – mode using a Bruker
D8 Advance X-ray diffractometer: Cu K1 irradiation,  = 1.5406 Å; room temperature (25 ºC); 2
= 4–80.
2. Compound characterization data
All known compounds were characterized by comparison of their physical and spectroscopic data
with those described in the literature (references are given between brackets). For new compounds,
copies of 1H- and 13-C-NMR graphical spectra are also provided.
1,3-Diynes (Table 2)
1,4-diphenyl-1,3-butadiyne [1]: white solid. IR (KBr) : 3050, 1485, 1440, 916, 760, 680, 530 cm1 1
. H-

.19-7.25 (m, 6H), 7.40-7.42 (m, 4H).
13
C-

= 73.9 (2Csp), 81.5
(2Csp), 121.6 (2C), 128.3 (4CH), 129.1 (2CH), 132.3 (4CH). MS: m/z = 202 (M+, 100%), 203 (17),
201 (11), 200 (20).
1,4-di-p-tolylbuta-1,3-diyne [2]: beige solid. IR (film) : 3060, 2988, 2133, 1267, 751 cm-1. 1HRMN:
= 2.39 (s, 6H, 2CH3), 7.25 (d, J = 11.0 Hz, 4H), 7.42 (d, J = 11.0 Hz, 4H). 13C-RMN: 
= 21.6 (2CH3), 73.4 (2Csp), 81.5 (2Csp), 118.8 (2C-Csp), 129.2 (2CH), 132.4 (2CH), 139.5 (2CCH3). MS: m/z = 230 (M+, 100%).
3
1,4-bis(p-N,N-dimethylaminophenylethynyl)-1,3-butadiyne [1]: brown solid. IR (film) : 3065,
2951, 1603, 807 cm-1. 1H-RMN:
= 8.9 Hz, 4H). 13C-RMN:


= 2.90 (s, 12H, 4CH3-N), 6.53 (d, J = 8.9 Hz, 4H), 7.30 (d, J
= 40.4 (4CH3-N), 73.1 (2Csp), 82.7 (2Csp), 109.1 (2C), 112.1 (4CH),
134.0 (4CH), 150.7 (2C-N). MS: m/z = 288 (M+, 100%), 289 (21), 273 (13), 272 (16), 144 (15), 143
(18).
7,9-hexadecadiyne [3]: colorless oil. IR (film) : 2924, 2120, 1216, 1170 cm-1. 1H-RMN: 
=
0.87 (t, J = 6.6 Hz, 6H, 2CH3), 1.20-1.40 (m, 12H, 6CH2), 1.47-1.53 (m, 4H, 2CH2), 2.22 (t, J = 6.8
Hz, 4H, 2CH2-Csp). 13C-RMN: 
= 14.4 (2CH3), 19.6 (2CH2-Csp), 22.9 (2CH2), 28.7 (2CH2), 28.9
(2CH2), 31.7 (2CH2), 65.7 (2Csp), 77.9 (2Csp). MS: m/z = 218 (M+, 0.15%), 133 (20), 119 (37), 117
(15), 115 (12), 107 (24), 106 (11), 105 (57), 103 (13), 95 (23), 93 (40), 92 (18), 91 (100), 81 (30),
80 (10), 79 (55), 78 (32), 77 (44), 76 (15), 69 (13), 67 (39), 65 (22), 63 (17), 55 (31), 51 (20), 43
(42), 41 (71), 39 (29).
11,13-tetracosadiyne [3]: colorless liquid. IR (film) : 2955, 2928, 2846, 1460 cm-1. 1H-RMN: 
= 0.81 (t, J = 6.5 Hz, 6H, 2CH3), 1.19-1.28 (m, 28H, 14CH2), 1.41-1.46 (m, 4H, 2CH2), 2.15 (t, J
= 6.8 Hz, 4H, 2CH2-Csp). 13C-RMN: 
= 14.0 (2CH3), 19.2 (2CH2-Csp), 22.6 (2CH2), 28.4 (2CH2),
28.8 (2CH2), 29.1 (2CH2), 29.3 (2CH2), 29.4 (2CH2), 29.5 (2CH2), 31.9 (2CH2), 65.4 (2Csp), 77.3
(2Csp). MS: m/z = 330 (M+, 0.1%), 175 (10), 161 (18), 147 (21), 135 (17), 134 (13), 133 (35), 121
(41), 120 (12), 119 (40), 117 (20), 115 (11), 109 (15), 107 (31), 105 (45), 103 (10), 95 (39), 94 (16),
93 (44), 92 (20), 91 (89), 83 (15), 81 (54), 80 (17), 79 (62), 78 (23), 77 (30), 69 (27), 67 (58), 65
(14), 57 (27), 55 (54), 43 (97), 42 (11), 41 (100), 39 (17).
1,4-di(1-ciclohexenyl)-1,3-butadiyne [3]: white solid. IR (KBr) : 2932, 2854, 1615, 908 cm-1. 1HRMN: 
= 1.57-1.66 (m, 8H, 4CH2), 2.10-2.12 (m, 8H, 4CH2), 6.25 (t, J = 4.0 Hz, 2H, 2CHolefinic).
4
C-RMN: 
13
= 21.7 (2CH2), 22.5 (2CH2), 26.2 (2CH2-CHolefinic), 29.1(2CH2-C), 72.0 (2Csp), 83.0
(2Csp), 120.4 (2C), 138.3 (2CHolefinic). MS: m/z = 210 (M+, 100%), 167 (32), 141 (19), 77(10).
1,8-diphenyl-3,5-octadiyne [3]: beige solid. 1H-RMN:

= 2.40 (t, J = 7.4 Hz, 4H, 2CH2-Csp),
2.70 (t, J = 7.4 Hz, 4H, 2CH2), 7.06-7.18 (m, 10H). 13C-RMN: 
3 (2CH2-Csp), 34.5 (2CH2),
65.9 (2Csp), 76.8 (2Csp), 126.3 (2CH), 128.2 (4CH), 128.3 (4CH), 140.0 (2C). MS: m/z = 258 (M+,
7%), 167 (19), 165 (26), 152 (17), 117 (11), 91 (100), 65 (22).
1,2,3-Triazoles (Table 4)
1-benzyl-4-phenyl-1H-1,2,3-triazole [4]: white solid. IR (KBr) : 3103, 2927, 1454, 1431, 1251,
1070 cm-1. 1H-RMN: 
(m, 2H).
13
C-RMN: 
= 5.37 (s, 2H, CH2), 7.13-7.23 (m, 8H), 7.75 (s, 1H, CHtriazole), 7.82-7.86
= 53.9 (CH2), 119.5 (CH), 125.4 (2CH), 127.8 (2CH), 127.9 (CH), 128.6
(3CH), 128.9 (2CH), 130.3 (C), 134.5 (C), 147.9 (C-N). MS: m/z = 235 (M+, 28%), 206 (78), 180
(14), 179 (11), 116 (100), 104 (20), 91 (70), 80 (27), 65 (15).
1-benzyl-4-(4-bromophenyl)-1H-1,2,3-triazole [5]: beige solid. IR (KBr) : 3117, 3069, 3040,
2950, 1606, 1551, 1478, 1207, 1090, 1051, 977, 809, 723, 707, 659 cm-1. 1H-RMN: 
= 5.45 (s,
2H, CH2), 7.19-7.21 (m, 2H), 7.27-7.29 (m, 3H), 7.39-7.41 (m, 2H), 7.55-7.58 (m, 3H). 13C-RMN:

= 54.1 (CH2), 119.5 (CH), 121.8 (C-Br), 127.0 (2CH), 127.9 (2CH), 128.7 (CH), 129.0 (2CH),
129.4 (C), 131.8 (2CH), 134.3 (C), 147.0 (C-N).
5
4-(1-benzyl-1H-1,2,3-triazol-4-yl)-N,N-dimethylaniline [5]: brown solid. 1H-RMN: 
= 2.91 (s,
6H, 2CH3-N), 5.48 (s, 2H, CH2), 6.67 (d, J = 8.9 Hz, 2H), 7.16-7.37 (m, 5H), 7.46 (s, 1H, CHtriazole),
7.60 (d, J = 8.9 Hz, 2H).
C-RMN: 
13
= 40.6 (2CH3-N), 54.2 (CH2), 112.5 (2CH), 118.9 (C),
126.8 (CH), 128.1 (2CH), 128.8 (2CH), 129.2 (3CH), 135.1 (C), 148.9 (Ctriazole), 150.5 (CN(CH3)2). MS: m/z = 278 (M+, 42%), 250 (29), 249 (100), 235 (15), 233 (15), 222 (32), 207 (20),
206 (21), 173 (31), 159 (35), 144 (16), 143 (26), 116 (12), 91 (34), 89 (16), 77 (10), 65 (15), 63
(10).
1-benzyl-4-butyl-1H-1,2,3-triazole [6]: white solid. IR (KBr) : 3109, 2988, 2845, 1576, 1475,
1135, 789, 684 cm-1. 1H-RMN: 
= 0.83 (t, J = 6.6 Hz, 3H, CH3), 1.27-1.31 (m, 2H, CH2), 1.52-
1.57 (m, 2H, CH2), 2.61 (t, J = 7.0 Hz, 2H, CH2-Ctriazole), 5.41 (s, 2H, CH2-N), 7.11-7.27 (m, 6H).
C-RMN: 
13
= 13.7 (CH3), 22.2 (CH2), 25.3 (CH2), 31.4 (CH2), 53.8 (CH2N), 120.4 (CH), 127.8
(2CH), 128.4 (CH), 128.9 (2CH), 134.9 (C), 148.8 (C-N). MS: m/z = 215 (M+, 2%), 173 (7), 144
(5), 130 (4), 104 (6), 91 (100), 69 (4), 65 (12), 41 (10).
1-benzyl-4-cyclohexyl-1H-1,2,3-triazole [4]: white solid. IR (KBr) : 3142, 2924, 2844, 1598,
1502, 1447, 1221, 1044, 995, 805, 756, 692 cm-1. 1H-RMN: 
= 1.29-1.95 (m, 10H, 5CH2), 2.67
(bs, 1H, CH), 5.41 (s, 2H, CH2-N), 7.08-7.28 (m, 6H). 13C-RMN: 
= 26.0 (3CH2), 32.9 (2CH2),
35.2 (CH), 53.9 (CH2-N), 119.1 (CH), 127.9 (2CH), 128.4 (CH), 128.9 (2CH), 134.9 (C), 154.1 (CN). MS: m/z = 241 (M+, 12%), 122 (13), 91 (100).
6
1-benzyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1H-1,2,3-triazole: pale yellow liquid. IR
(film) : 3133, 3053, 2941, 2859, 1723, 1494, 1445, 1036, 726, 713 cm-1. 1H-RMN: 
= 1.40-1.72
(m, 6H, 3CH2), 3.41-3.47 (m, 1H, O-CHH-CH2), 3.76-3.83 (m, 1H, O-CHH-CH2), 4.54 (d, J = 12.3
Hz, 1H, O-CHH-Ctriazole), 4.64-4.67 (m, 1H, CH-O), 4.77 (d, J = 12.3 Hz, 1H, O-CHH-Ctriazole), 5.43
(s, 2H, CH2-N), 7.19-7.21 (m, 2H), 7.28-7.31 (m, 3H), 7.40 (s, 1H, CHtriazole). 13C-RMN: 
= 19.2
(CH-CH2-CH2), 25.2 (O-CH2-CH2), 30.3 (CH-CH2), 54.0 (CH2-N), 60.5 (CH2-O), 62.2 (CH2-CH2O), 98.1 (CH-O), 122.3 (CH), 128.0 (2CH), 128.6 (CH), 128.9 (2CH), 134.3 (C), 145.4 (C-N). MS:
m/z = 273 (M+, 0.03%), 173 (24), 144 (31), 91 (100), 85 (16), 65 (14), 57 (8). HRMS (EI): m/z
calcd. for C15H19N3O2 273.1477; found 273.1484.
7
1-(4-methylbenzyl)-4-phenyl-1H-1,2,3-triazole [7]: brown solid. IR (film) : 3088, 2922, 2857,
1614, 1514, 1454, 1352, 1045, 976, 918, 833, 762, 697 cm-1. 1H-RMN: 
= 2.35 (s, 3H, CH3),
5.52 (s, 2H, CH2), 7.17-7.21 (m, 4H), 7.28-7.31 (m, 1H), 7.38 (dd, J = 1.7 Hz y J = 8.0 Hz, 2H),
7.62 (s, 1H, CHtriazole), 7.79 (d, J = 8.0 Hz, 2H). 13C-RMN:  = 21.0 (CH3), 53.9 (CH2), 119.3 (CH),
125.0 (2CH), 128.0 (3CH), 128.7 (2CH), 129.7 (2CH), 130.5 (C), 131.5 (C), 138.6 (C), 148.0 (CN). MS: m/z = 249 (M+, 29%), 221 (13), 220 (63), 206 (17), 179 (18), 118 (20), 117 (21), 116 (100),
105 (74), 103 (15), 89 (24), 79 (15), 77 (22).
1-(2-nitrobenzyl)-4-phenyl-1H-1,2,3-triazole [8]: yellow solid. IR (KBr) : 3126, 3086, 2930,
2857, 1605, 1519, 1465, 1433, 1108, 1078, 1041, 1022, 841, 808, 768, 733, 696 cm-1. 1H-RMN: 
8
= 5.91 (s, 2H, CH2), 7.05-8.07 (m, 10H).
13
C-RMN: 
= 50.8 (CH2), 120.6 (CH), 125.3 (CH),
125.6 (2CH), 128.3 (CH), 128.8 (2CH), 129.5 (CH), 130.2 (CH), 130.7 (C), 134.3 (CH), 147.3 (CN), 148.2 (C-NO2), falta un c. MS: m/z = 280 (M+ ??), 116 (100).
4-phenyl-1-(4-vinylbenzyl)-1H-1,2,3-triazole [9]: palid yellow solid. IR (film) : 3088, 3044,
2959, 1517, 1442, 918, 857, 779, 764, 738, 716, 692 cm-1. 1H-RMN: 
= 5.31 (d, J = 10.9 Hz, 1H,
CHHolefinic), 5.52 (s, 2H, CH2), 5.78 (d, J = 17.5 Hz, 1H, CHHolefinic), 6.68-6.77 (m, 1H, CHolefinic),
7.25-7.27 (m, 2H), 7.33-7.42 (m, 7H), 7.70 (s, 1H, CHtriazole). 13C-RMN: 
= 53.7 (CH2), 114.77
(CH2,olefinic), 119.51 (CH), 125.52 (2CH), 126.69 (2CH), 128.03 (CH), 128.13 (2CH), 128.65
(2CH), 130.24 (C), 133.83 (C), 135.79 (CH), 137.89 (C), 147.97 (C-N).
1-(4-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole [10]: white solid. IR (KBr) : 3129, 3044, 2924,
2844, 1612, 1461, 1241, 1180, 1107, 1078, 1035, 975, 911, 845, 816, 756, 695 cm-1. 1H-RMN: 
= 3.78 (s, 3H, CH3O), 5.45 (s, 2H, CH2), 6.86-6.91 (m, 2H), 7.24-7.30 (m, 3H), 7.37-7.40 (m,
2H), 7.67 (s, 1H, CHtriazole), 7.78-7.80 (m, 2H).
13
C-RMN: 
= 53.4 (CH2), 55.1 (OCH3), 114.2
(2CH), 119.3 (CH), 125.4 (2CH), 127.9 (CH), 128.5 (2CH), 129.4 (2CH), 130.3 (C), 133.2 (C),
147.8 (C-N), 159.6 (C-OCH3).
1-nonyl-4-phenyl-1H-1,2,3-triazole [11]: pale yellow solid. IR (KBr) : 3136, 3088, 2971, 2900,
2854, 1470, 1068 cm-1. 1H-RMN: 
= 0.80 (t, J = 6.1 Hz, 3H, CH3), 1.19-1.27 (m, 12H, 6CH2),
1.85-1.89 (m, 2H, CH2-CH2N), 4.32 (t, J = 7.2 Hz, 2H, CH2N), 7.19-7.37 (m, 3H), 7.67 (s, 1H,
CHtriazole), 7.76 (d, J = 8.0 Hz, 2H).
C-RMN: 
13
= 14.0 (CH3), 22.6 (CH2), 26.4 (CH2), 28.9
(CH2), 29.1 (CH2), 29.3 (CH2), 30.3 (CH2), 31.7 (CH2), 50.4 (CH2N), 119.3 (CH), 125.6 (2CH),
9
128.0 (CH), 128.7 (2CH), 130.7 (C), 147.6 (C-N). MS: m/z = 271 (M+, 19%), 242 (19), 172 (24),
158 (12), 145 (31), 144 (20), 130 (18), 118 (14), 117 (100), 116 (30), 104 (33), 103 (19), 102 (23),
91 (17), 90 (13), 89 (23), 77 (14), 57 (11), 55 (20).
Propargylamines (Table 6)
4-(1,3-diphenylprop-2-yn-1-yl)morpholine [12]: orange liquid. IR (film) : 3039, 2962, 2862,
1596, 1496, 1442, 1319, 1280, 1118, 1010, 748, 686 cm-1. 1H-RMN: 
= 2.56 (t, J = 4.3 Hz, 4H,
2CH2-N), 3.61-3.69 (m, 4H, 2CH2-O), 4.72 (s, 1H, CH-N), 7.21-7.56 (m, 10H).
C-RMN: 
13
=
49.7 (2CH2-N), 61.9 (CH-N), 67.0 (2CH2-O), 84.9 (Csp), 88.4 (Csp), 122.8 (C), 127.7 (CH), 128.1
(2CH), 128.2 (3CH), 128.5 (2CH), 131.7 (2CH), 137.5 (C). MS: m/z = 277 (M+, 29%), 191 (100),
86 (47), 56 (80).
4-(1-phenyl-3-(p-tolyl)prop-2-yn-2-yl)morpholine [13]: colorless liquid. IR (film) : 3048, 2972,
2308, 1592 cm-1. 1H-RMN: 
= 2.36 (s, 3H, CH3), 2.60 (m, 4H, 2CH2-N), 3.70-3.74 (m, 4H, CH2-
O), 4.79 (s, 1H, CH-N), 7.13-7.16 (m, 2H), 7.30-7.43 (m, 5H), 7.62-7.65 (m, 2H).
13
C-RMN: =
21.4 (CH3), 49.7 (2CH2-N), 61.9 (CH-N), 67.1 (2CH2-O), 84.1 (Csp), 88.5 (Csp), 119.8 (C-Csp),
127.6 (CH), 128.1 (2CH), 128.5 (2CH), 129.0 (2CH), 131.6 (2CH), 137.8 (C-CH3), 138.2 (C). MS:
m/z = 291 (M+, 14%), 214 (14), 206 (18), 205 (100), 202 (12).
10
4-(3-(cyclohex-1-en-1-yl)-1-phenylprop-2-yn-1-yl)morpholine: pale yellow liquid. IR (film) :
3063, 3022, 2932, 2851, 2818, 1645, 1605, 1490, 1453, 730, 701 cm-1. 1H-RMN: 
= 1.59-1.67
(m, 4H, 2CH2), 2.10-2.12 (m, 2H, CH2), 2.18-2.20 (m, 2H, CH2), 2.56 (t, J = 4.5 Hz, 4H, 2CH2-N),
3.65-3.76 (m, 4H, 2CH2-O), 4.68 (s, 1H, CH-N), 6.17-6.18 (m, 1H, CHolefinic), 7.27-7.41 (m, 3H),
7.56 (d, J = 7.2 Hz, 2H).
C-RMN:  = 21.4 (CH2), 22.2 (CH2), 25.5 (CH2), 29.5 (CH2), 49.6
13
(2CH2-N), 61.8 (CH-N), 67.0 (2CH2-O), 81.8 (Csp), 90.3 (Csp), 120.3 (C), 127.5 (CH), 128.0
(2CH), 128.5 (2CH), 134.6 (CH), 138.0 (C). MS: m/z = 281 (M+, 29%), 208 (15), 204 (39), 196
(20), 195 (100), 179 (10), 167 (19), 166 (11), 165 (28), 153 (13), 152 (15), 115 (22), 91 (21), 86
(18), 77 (10), 56 (14). HRMS (EI): m/z calcd. for C19H23NO 281.1780; found 281.1775.
11
4-(1-phenyltridec-2-yn-1-yl)morpholine: orange liquid. IR (film) : 3063, 3026, 2928, 2851,
1600, 1486, 713, 697 cm-1. 1H-RMN: 
= 0.80 (t, J = 6.8 Hz, 3H, CH3), 1.19-1.38 (m, 14H,
7CH2), 1.45-1.55 (m, 2H, CH2-CH2-Csp), 2.23 (t, J = 6.5 Hz, 2H, CH2-Csp), 2.47 (t, J = 4.2 Hz, 4H,
2CH2-N), 3.57-3.71 (m, 4H, 2CH2-O), 4.48 (s, 1H, CH-N), 7.16-7.38 (m, 3H), 7.47 (d, J = 7.1 Hz,
2H). 13C-RMN: 
= 14.0 (CH3), 18.7 (CH2), 22.6 (CH2), 28.8 (CH2), 28.9 (CH2), 29.0 (CH2), 29.2
(CH2), 29.5 (2CH2), 31.8 (CH2), 49.6 (2CH2-N), 61.5 (CH-N), 66.9 (2CH2-O), 75.2 (Csp), 88.7
(Csp), 127.5 (CH), 127.9 (2CH), 128.5 (2CH), 138.1 (C). MS: m/z = 341 (M+, 8%), 264 (82), 189
(9), 175 (11), 161 (19), 148 (10), 147 (21), 141 (12), 135 (16), 134 (12), 133 (32), 131 (12), 129
(22), 128 (27), 121 (36), 120 (12), 119 (37), 117 (33), 115 (23), 109 (14), 107 (28), 106 (12), 105
(44), 103 (11), 95 (35), 94 (14), 93 (38), 92 (19), 91 (100), 86 (23), 83 (13), 82 (11), 81 (45), 80
(13), 79 (54), 78 (21), 77 (30), 69 (23), 67 (47), 65 (13), 57 (26), 56 (22), 55 (49). HRMS (EI): m/z
calcd. for C23H35NO 341.2719; found 341.2727.
12
13
4-(1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-yl)morpholine [13]: orange liquid. IR (film) :
3045, 2962, 2312, 1594, 1349, 1190, 1017, 713 cm-1. 1H-RMN:  = 2.48-2.59 (m, 4H, 2CH2-N),
3.63-3.66 (m, 4H,2CH2-O), 3.71 (s, 3H, OCH3), 4.66 (s, 1H, CH-N), 6.79-6.82 (m, 2H), 7.22-7.24
(m, 3H), 7.40-7.46 (m, 4H).
13
C-RMN: 
= 49.6 (2CH2-N), 55.1 (OCH3), 61.3 (CH-N), 66.9
(2CH2-O), 85.2 (Csp), 88.1 (Csp), 113.4 (2CH), 122.8 (C), 128.1 (CH), 128.2 (2CH), 129.6 (2CH),
131.6 (2CH y C), 159.1 (C-OCH3). MS: m/z = 307 (M+, 7.6%), 222 (18), 221 (100), 178 (11).
4-(5,9-dimethyl-1-phenyldec-8-en-1-yn-3-yl)morpholine: yellow liquid. IR (film) : 3070, 3030,
2953, 2920, 2851, 2818, 1494, 1449, 1118, 750, 689 cm-1. 1H-RMN:  = 0.99 (d, J = 6.4 Hz, 3H,
CH3-CH), 1.18-1.28 (m, 1H, CH-CH3), 1.42-1.82 (m, 10H, 2CH3 y 2CH2), 1.98-2.08 (m, 2H, CH2),
2.55-2.61 (m, 2H, CH2-N), 2.72-2.78 (m, 2H, CH2-N), 3.63 (t, J = 7.4 Hz, 1H, CH-Csp), 3.71-3.83
(m, 4H, 2CH2-O), 5.11-5.16 (m, 1H, CHolefinic), 7.30-7.32 (m, 3H), 7.43-7.47 (m, 2H).

13
C-RMN:
= 17.6 (CH3), 19.7 (CH3), 25.3 (CH2), 25.6 (CH3), 29.3 (CH3-CH), 36.6 (CH2), 39.8 (CH2), 49.6
(2CH2-N), 55.7 (CH-N), 67.1 (2CH2-O), 86.0 (Csp), 87.3 (Csp), 123.2 (C), 124.7 (CH), 127.8 (CH),
128.1 (2CH), 131.1 (C(CH3)2), 131.6 (2CH). MS: m/z = 325 (M+, 0.15%), 201 (15), 200 (100), 115
(17), 41 (16). HRMS (EI): m/z calcd. for C22H31NO 325.2406; found 325.2410.
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1-(1,3-diphenylprop-2-yn-1-yl)pyrrolidine [13]: brown liquid. IR (film) : 3040, 2965, 2807,
2694, 2278, 1619, 1520, 1411, 1338, 1175, 756 cm-1. 1H-RMN: 
= 1.87 (t, J = 5.9 Hz, 4H,
2CH2), 2.82-2.90 (m, 4H, 2CH2-N), 5.12 (s, 1H, CH-N), 7.33-7.68 (m, 10H).
13
C-RMN: = 23.4
(2CH2), 49.9 (2CH2-N), 58.7 (CH), 85.6 (Csp), 87.3 (Csp), 122.7 (C), 127.8 (CH), 127.9 (CH), 128.2
(2CH), 128.3 (2CH), 128.5 (2CH), 131.7 (2CH), 138.1 (C). MS: m/z = 261 (M+, 18%), 260 (12),
192 (23), 191 (100), 189 (26), 184 (58), 115 (13).
N,N-diethyl-1-phenyl-3-(p-tolyl)prop-2-yn-2-amine [14]: brown liquid. IR (film) : 3090, 3060,
2930, 2870, 1500, 1470, 1430, 747 cm-1. 1H-RMN: 
= 1.08 (t, J = 7.2 Hz, 6H, 2CH3CH2), 2.36
(s, 3H, CH3), 2.50-2.59 (m, 2H, CH2), 2.60-2.69 (m, 2H, CH2), 5.05 (s, 1H, CH-N), 7.14 (d, J = 7.6
Hz, 2H), 7.28 (t, J = 7.6 Hz, 1H), 7.35 (t, J = 7.6 Hz, 2H), 7.40 (d, J = 7.6 Hz, 2H), 7.69 (d, J = 7.6
Hz, 2H).
13
C-RMN: = 13.5 (2CH3CH2), 21.4 (CH3), 44.5 (2CH2), 56.9 (CH-N), 85.1 (Csp), 87.5
(Csp), 99.9 (C), 120.2 (CH), 127.2 (2CH), 128.0 (2CH), 128.4 (2CH), 129.0 (2CH), 131.6 (C), 138.1
(C). MS: m/z = 277 (M+, 8.4%), 206 (18), 205 (100), 202 (10), 200 (26).
3. References
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[8] V. Calderone, I. Giorgi, O. Livi, E. Martinotti, A. Martelli, A. Nardi, II Farmaco 60 (2005) 367375.
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[12] M. J. Albaladejo, F. Alonso, Y. Moglie, M. Yus, Eur. J. Org. Chem. (2012) 3093-3104.
[13] M. Kidwai, A. Jahan, J. Iran. Chem. Soc. 8 (2011) 462-469.
[14] Z. Lin, D. Yu, Y. Zhang, Tetrahedron Lett. 52 (2011) 4967-4970.